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Title: Palladium-catalyzed condensation of N-aryl imines and alkynylbenziodoxolones to form multisubstituted furans
Authors: Lu, Beili
Wu, Junliang
Yoshikai, Naohiko
Keywords: DRNTU::Science::Chemistry::Organic chemistry
Issue Date: 2014
Source: Lu, B., Wu, J., & Yoshikai, N. (2014). Palladium-catalyzed condensation of N-aryl imines and alkynylbenziodoxolones to form multisubstituted furans. Journal of the American chemical society, 136(33), 11598-11601.
Series/Report no.: Journal of the American chemical society
Abstract: A palladium(II) catalyst promotes condensation of an N-aryl imine and an alkynylbenziodoxolone derivative to afford a multisubstituted furan, whose substituents are derived from the alkynyl moiety (2-position), the imine (3- and 4-positions), and the 2-iodobenzoate moiety (5-position), along with an N-arylformamide under mild conditions. The 2-iodophenyl group of the furan product serves as a versatile handle for further transformations. A series of isotope-labeling experiments shed light on the bond reorganization process in this unusual condensation reaction, which includes cleavage of the C–C triple bond and fragmentation of the carboxylate moiety.
DOI: 10.1021/ja5059795
Rights: © 2014 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by Journal of the American Chemical Society, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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